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Sciadonic acid

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Eicosatrienoic Acid, more commonly referred to as Sciadonic acid is a polyunsaturated fatty acid. In regard to its structure, 5Z,11Z,14Z-eicosa-5,11,14-trienoic acid (sciadonic acid) has 3 double bonds in the 5, 11, and 14 positions all of which are in the cis- conformation. It is further classified as Δ5-fatty, and an omega-6 acid due to the methylene interrupted double bond at carbon-5 and a final double bond 6 carbons away from the methylene tail of the hydrocarbon. Sciadonic acid is a naturally occurring compound and has been found to play a role as a plant metabolite, commonly found in pine nut oil.[3]. Furthermore, there have been propositions of several health applications for sciadonic acid as an anti-inflammatory agent. Sharing close structural similarity to arachidonic acid, sciadonic acid acts as a replacement phospholipid in the corresponding biochemical pathways.

Eicosatrienoic Acid[1][2]
Names
IUPAC name
(5Z, 11Z, 14Z)-icosa-5,11,14-trienoic acid
Other names
  • Sciadonic acid
  • 5Z, 11Z, 14Z-eicosatrienoic acid
  • All-cis-5,11,14-eicosatrienoic acid
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • Canonical: CCCCCC=CCC=CCCCCC=CCCCC(=O)O
  • Isomeric: CCCCC/C=C\C/C=C\CCCC/C=C\CCCC(=O)O
Properties
C20H34O2
Molar mass 306.490 g·mol−1
Density 0.9 g·cm−3
Boiling point 432 °C (810 °F; 705 K)
log P 7.59
1.489
Hazards
Flash point 329 °C (624 °F; 602 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Etymology

The root behind the nomenclature of sciadonic acid comes from its high abundance in the seed, leaves, and wood oils of the plant species Sciadopitys verticillate.[4]

Synthetic Methods

There are a few methods reagarding the synthesis of sciadonic acid and other Δ5-fatty acids. One method is through desaturase enzyme complexes in which the biosynthesis of sciadonic acid has been achieved in the organism Anemone leveillei via two Δ5-desaturases, AL10 and AL21.[5] Both desaturases have shown success in the synthesis of sciadonic acid, however, the mechanisms show different substrate specificity. AL21 has broad substrate specificity and acts on both saturated (16:0 and 18:0) and unsaturated (20:2, n-6) fatty acids.[6] In contrast AL10 has a much greater substrate specificity binding only to a C20 unsaturated fatty acid (20:2, n-6) When AL10 is co-expressed with a Δ9-elongase the biosynthesis of sciadonic acid is achieved in transgenic plants. A second synthetic method is achieved through an esterification reaction catalyzed via Lipozyme RM IM and pine nut oil. Lipase-catalyzed esterification reactions leading to the development of Δ5-fatty acids can be achieved in solvent-free conditions using water-jacketed vessel.[7]

Phylogenetic Significance in Gymnosperms

Sciadonic acid and several other Δ5-olefinic acids are found to be relatively abundant in gymnosperms. Setaria verticillata seeds and their fatty acid compositions allow for distinction between different Coniferophytes such as species from families such as Cupressaceae and Taxodiaceae.[8][9][10]. Sciadonic acid is a distinctive fatty acid that shows presence in the oils of seeds, leaves, and woods of conifers. Indicating that plant families can be characterized by the fatty acid composition of their seed, leaves, and wood oils.

Health Implications

Eicosanoids and metabolites found to be biologically active have correlated to tumor progression by several mechanisms such as interruption of cell signaling. In humans, fatty acid desaturases, FADS 1,2 and 3 are enzyme coding genes found in chromosome 11q13, in which alterations can be attributed to several types of cancers such as breast, ovarian and cervical cancer. In particular, the FADS2 enzyme, responsible for Δ6 desaturation is no longer functional.[11] In healthy tissues sciadonic acid is not within detectable concentrations however in human breast cancer tissues detectable concentrations have been found. Sciadonic acids structural similarity has shown potential as a substitute for arachidonic acid in cellular phospholipid pools in the signaling pathways.[12][13]In keratinocytes, sciadonic acids release from the cellular membrane phospholipid pool reduces levels of pro-inflammatory arachidonic acid and the corresponding pro-inflammatory down-stream mediator prostaglandin E2.[14] Reduction of pro-inflammatory mediator molecules is also occurs in murine macrophages, regulating the activation of NF-κΒ and MAPK pathways.[15]

References

  1. ^ U.S. National Library of Medicine. (n.d.). Sciadonic acid. National Center for Biotechnology Information. PubChem Compound Database. Retrieved November 10, 2022, from https://pubchem.ncbi.nlm.nih.gov/compound/Sciadonic-acid
  2. ^ Sciadonic acid. ChemSpider. (n.d.). Retrieved November 10, 2022, from http://www.chemspider.com/Chemical-Structure.392828.html
  3. ^ U.S. National Library of Medicine. (n.d.). Sciadonic acid. National Center for Biotechnology Information. PubChem Compound Database. Retrieved November 10, 2022, from https://pubchem.ncbi.nlm.nih.gov/compound/Sciadonic-acid
  4. ^ Wolff, R. L. (1999). All-CIS 5,11,14-20:3 acid: Podocarpic acid or sciadonic acid? Journal of the American Oil Chemists' Society, 76(10), 1255–1256. https://doi.org/10.1007/s11746-999-0102-7
  5. ^ Sayanova O, Haslam R, Venegas Caleron M, Napier JA. Cloning and characterization of unusual fatty acid desaturases from Anemone leveillei: identification of an acyl-coenzyme A C20 Delta5-desaturase responsible for the synthesis of sciadonic acid. Plant Physiol. 2007 May;144(1):455-67. doi: 10.1104/pp.107.098202. Epub 2007 Mar 23. PMID: 17384161; PMCID: PMC1913799.
  6. ^ Sayanova O, Haslam R, Venegas Caleron M, Napier JA. Cloning and characterization of unusual fatty acid desaturases from Anemone leveillei: identification of an acyl-coenzyme A C20 Delta5-desaturase responsible for the synthesis of sciadonic acid. Plant Physiol. 2007 May;144(1):455-67. doi: 10.1104/pp.107.098202. Epub 2007 Mar 23. PMID: 17384161; PMCID: PMC1913799.
  7. ^ Kim, H., Choi, N., Kim, H.-R., Lee, J., & Kim, I.-H. (2018). Preparation of high purity Δ5-olefinic acids from pine nut oil via repeated lipase-catalyzed esterification. Journal of Oleo Science, 67(11), 1435–1442. https://doi.org/10.5650/jos.ess18136
  8. ^ Wolff, R. L. (1999). The phylogenetic significance of sciadonic (all-cis 5,11,14-20:3) acid in gymnosperms and its quantitative significance in land plants. Journal of the American Oil Chemists' Society, 76(12), 1515–1516. https://doi.org/10.1007/s11746-999-0195-z
  9. ^ 73:765–771 (1996). 14. Wolff, R.L., L.G. Deluc, A.M. Marpeau, and B. Comps, Chemotaxonomic Differentiation of Conifer Families and Genera Based on the Seed Oil Fatty Acid Compositions: Multivariate Analyses, Trees 12:57–65 (1997)
  10. ^ Wolff, R.L., Clarification on the Taxonomic Position of Sciadopitys verticillata Among Coniferophytes Based on the Seed Oil Fatty Acid Compositions, J. Am. Oil Chem. Soc. 75:757–758 (1998)
  11. ^ Park, H. G., Zhang, J. Y., Foster, C., Sudilovsky, D., Schwed, D. A., Mecenas, J., Devapatla, S., Lawrence, P., Kothapalli, K. S. D., & Brenna, J. T. (2018). A rare eicosanoid precursor analogue, sciadonic acid (5Z,11z,14Z–20:3), detected in vivo in hormone positive breast cancer tissue. Prostaglandins, Leukotrienes and Essential Fatty Acids, 134, 1–6. https://doi.org/10.1016/j.plefa.2018.05.002
  12. ^ Park, H. G., Zhang, J. Y., Foster, C., Sudilovsky, D., Schwed, D. A., Mecenas, J., Devapatla, S., Lawrence, P., Kothapalli, K. S. D., & Brenna, J. T. (2018). A rare eicosanoid precursor analogue, sciadonic acid (5Z,11z,14Z–20:3), detected in vivo in hormone positive breast cancer tissue. Prostaglandins, Leukotrienes and Essential Fatty Acids, 134, 1–6. https://doi.org/10.1016/j.plefa.2018.05.002
  13. ^ Chen, S.-J., Huang, W.-C., Yang, T.-T., Lu, J.-H., & Chuang, L.-T. (2012). Incorporation of sciadonic acid into cellular phospholipids reduces pro-inflammatory mediators in murine [[macrophages through NF-ΚB and MAPK signaling pathways. Food and Chemical Toxicology, 50(10), 3687–3695. https://doi.org/10.1016/j.fct.2012.07.057
  14. ^ Chen, S.-J., Huang, W.-C., Yang, T.-T., Lu, J.-H., & Chuang, L.-T. (2012). Incorporation of sciadonic acid into cellular phospholipids reduces pro-inflammatory mediators in murine macrophages through NF-ΚB and MAPK signaling pathways. Food and Chemical Toxicology, 50(10), 3687–3695. https://doi.org/10.1016/j.fct.2012.07.057
  15. ^ Chen, S.-J., Huang, W.-C., Yang, T.-T., Lu, J.-H., & Chuang, L.-T. (2012). Incorporation of sciadonic acid into cellular phospholipids reduces pro-inflammatory mediators in murine macrophages through NF-ΚB and MAPK signaling pathways. Food and Chemical Toxicology, 50(10), 3687–3695. https://doi.org/10.1016/j.fct.2012.07.057
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